22509-60-0Relevant academic research and scientific papers
Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis
Hu, Long,Xu, Silin,Zhao, Zhenguang,Yang, Yang,Peng, Zhiyuan,Yang, Ming,Wang, Changliu,Zhao, Junfeng
, p. 13135 - 13138 (2016)
A highly efficient, two-step, one-pot synthetic strategy for amides and peptides was developed by employing ynamides as novel coupling reagents under extremely mild reaction conditions. The ynamides not only are effective for simple amide and dipeptide synthesis but can also be used for peptide segment condensation. Importantly, no racemization was detected during the activation of chiral carboxylic acids. Excellent amidation selectivity toward amino groups in the presence of -OH, -SH, -CONH2, ArNH2, and the NH of indole was observed, making the protection of these functional groups unnecessary in amide and peptide synthesis.
Mild and efficient preparation method of alpha-acyloxy alkenyl amide compound and application thereof to synthesis of amide and polypeptide
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Paragraph 0026; 0027, (2017/05/16)
The invention discloses a mild and efficient preparation method of an alpha-acyloxy alkenyl amide compound and application thereof to synthesis of an amide and a polypeptide. The alpha-acyloxy alkenyl amide compound is obtained by an addition reaction of alkyne amide and carboxylic acid in dichloromethane under a condition that the temperature is 0 to 50 DEG C; the product alpha-acyloxy alkenyl amide compound can generate the amide or the polypeptide with amides through combination reaction; the two reactions can be carried out step by step and can also be carried out in one pot; when the two reactions are carried out in one pot, the product alpha-acyloxy alkenyl amide compound does not need to be purified from the former reaction and the amide compound is directly added to react, wherein in the reaction of generating the amide or the polypeptide, a solvent can also be water, so that a novel method for fixed-site decoration and marking of biological macromolecules including proteins, nucleic acid and the like in a water phase is provided. The mild and efficient preparation method has moderate reaction conditions and does not need a metal catalyst; when the carboxylic acid, which has chirality on an alpha site of carboxyl, forms an amide bond or a peptide bond, no racemization occurs; the mild and efficient preparation method is simple to operate and wide in application range.
